Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate

Piotr Wałejko; Michał Dąbrowski; Lech Szczepaniak; Jacek W Morzycki; Stanisław Witkowski

doi:10.3762/bjoc.11.204

Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate

Beilstein J Org Chem. 2015 Oct 13:11:1893-901. doi: 10.3762/bjoc.11.204. eCollection 2015.

Authors

Piotr Wałejko¹, Michał Dąbrowski¹, Lech Szczepaniak¹, Jacek W Morzycki¹, Stanisław Witkowski¹

Affiliation

¹ Institute of Chemistry, University of Białystok, ul. Ciołkowskiego 1K, 15-245 Białystok, Poland.

Abstract

The ROCM reactions of exo- and endo-2-cyano-7-oxanorbornenes with allyl alcohol or allyl acetate promoted by different ruthenium alkylidene catalysts were studied. The stereochemical outcome of the reactions was established. The issues concerning chemo- (ROCM vs ROMP), regio- (1-2- vs 1-3-product formation), and stereo- (E/Z isomerism) selectivity of reactions under various conditions are discussed. Surprisingly good yields of the ROCM products were obtained under neat conditions.

Keywords: Grubbs’ catalysts; ROCM; ROMP; Z-selectivity; metathesis.